EP0456636B1 - A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent - Google Patents

A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent Download PDF

Info

Publication number
EP0456636B1
EP0456636B1 EP89908709A EP89908709A EP0456636B1 EP 0456636 B1 EP0456636 B1 EP 0456636B1 EP 89908709 A EP89908709 A EP 89908709A EP 89908709 A EP89908709 A EP 89908709A EP 0456636 B1 EP0456636 B1 EP 0456636B1
Authority
EP
European Patent Office
Prior art keywords
lactitol
monohydrate
temperature
lactitol monohydrate
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89908709A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0456636A1 (en
Inventor
Heikki Olavi HEIKKILÄ
Juha Veikko Nurmi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Suomen Xyrofin Oy
Original Assignee
Xyrofin Oy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8527497&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0456636(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Xyrofin Oy filed Critical Xyrofin Oy
Priority to DE8916202U priority Critical patent/DE8916202U1/de
Publication of EP0456636A1 publication Critical patent/EP0456636A1/en
Application granted granted Critical
Publication of EP0456636B1 publication Critical patent/EP0456636B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/52—Liquid products; Solid products in the form of powders, flakes or granules for making liquid products ; Finished or semi-finished solid products, frozen granules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/34—Sugar alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate

Definitions

  • the invention relates to a new crystalline lactitol monohydrate, and a process for the preparation thereof by crystallization from an aqueous solution, the use of the said new crystalline lactitol monohydrate in dietetic products, confectionery, bakery products, cereals, desserts, jams, beverages, chocolate, chewing gum and ice-cream, as well as in costmetic products, and in the manufacture a pharmaceutical , such as tooth paste.
  • the invention also relates to a new sweetening agent resembling sugar, mainly composed of the said new crystalline lactitol monohydrate.
  • Lactitol is a bulk sweetener which can be used as a total or partial replacement for sucrose, however, its energy content is only about half of that of sucrose, and it does not cause increased blood glucose content; furthermore, it is tooth-friendly (see Developments in Sweeteners, Ed. Grenby, T.H., Vol. 3, 1987, p. 65-81).
  • lactitol is prepared analogously with the preparation of sorbitol from glucose by hydrogenation in the presence of a Raney nickel catalyst.
  • An aqueous solution of lactose typically having a concentration between 30 and 40% by weight due to the poor solubility of lactose, is hydrogenated at 70 to 130°C at a pressure between 30 and 74 atm.
  • the preparation is described in Wolfrom, M.L., Burke, W.J., Brown, K.R. and Rose, R.S., J. Am. Chem. Soc. 60, (1938) p. 571-573.
  • Crystalline lactitol is reported to occur in anhydrous form (anhydride) as well as in the form of a monohydrate and dihydrate, which forms have been known for a long time with the exception of pure monohydrate.
  • lactitol monohydrate is of considerable commercial interest on account of its low hygroscopicity.
  • lactitol anhydride can be crystallized by adding ethanol to a lactitol solution evaporated to a high concentration. After a crystallization time of one month, the yield of lactitol was 80%, and the melting point of the resulting crystal, which was found to be an anhydride, was between 144 and 146°C.
  • the surface layer of said partially anhydrated monohydrate is imperfect and under suitable conditions it will be restored partially or completely to the monohydrate form. Since the formation of a perfect lattice structure is irreversible, the restored crystal structure will never be perfect, i.e. if the anhydride or partially anhydrated monohydrate takes (binds) crystal water, the product obtained does not have the crystal structure of lactitol monohydrate. Both the anhydrated and partially restored monohydrate easily get cloddy and have a rather poor flowability and rather a high hygroscopicity on account of the fragmented surface and high dust content of the product.
  • Monohydrate loses all of its crystal water as rapidly as in two hours when it is dried at 105°C in a conventional laboratory oven.
  • the "monohydrate” disclosed in this patent, which lost 2% of its weight at 130°C during 3 days, is originally a monohydrate anhydrated to a degree of anhydration of 60%.
  • the "monohydrates” disclosed in the European patent Are not monohydrates anhydrated from pure monohydrate; instead, they are overdried products formed from the mixtures of dihydrate and monohydrate due to the crystallization method.
  • Lactitol hydrate powders anhydrated to a moisture content of less than 3% have been prepared by drying both lactitol solution and crystalline hydrate. The hygroscopicity of these powders is utilized in drying moist mixtures (European Patent Application 0231643).
  • the new lactitol monohydrate has a good flowability and long shelf life, and it is stable at room temperatures, in relative humidities ranging from 25 to 75%. After having been stored under varying atmospheric conditions for about two years in an open paper sack, the lactitol monohydrate did not become cloddy and its flowability was 5.1 s/100 g measured by a funnel technique, the inclination of the funnel being 60°, the pipe length 23 mm and the inner diameter 11 mm.
  • the infrared absorption of the lactitol monohydrate was measured by a Perkin-Elmer 398 spectrometer from a tablet having a composition of 1 g of lactitol monohydrate and 131 g of KBr. The infrared spectrum is shown in the drawing.
  • melt When determining the melting point, one must take into account that molten lactitol monohydrate has a high viscosity at its melting temperature, wherefore it takes time (even 2 minutes) before the sample is spread evenly on the walls of the capillary tube. Furthermore, the melt often contains bubbles caused by the liberation of crystal water, which remain in the melt for a long time.
  • lactitol monohydrate anhydride is prepared by crystallizing lactitol within the temperature range from 10 to 50°C from a seeded lactitol solution obtained by hydrogenation and evaporated to a concentration between 70 and 85% or from a mother liquor obtained from the first crystallization step.
  • This process can be used for the crystallization of lactitol only when the purity of lactitol in the feed solution is high, and since dihydrate may already be crystallized from pure lactitol solution, the crystallization of pure monohydrate is difficult if not impossible.
  • crystallization temperatures in the range from 80 to 30°C are considerably higher than in the prior art process (from 50 to 10°C), whereby it is possible to crystallize lactitol monohydrate in at least four successive crystallization steps.
  • the total yield of lactitol monohydrate is considerably higher than can be achieved with the prior art process (no more than 85% on lactitol).
  • the crystallization tests showed that if the crystallization is to occur in a controlled manner for obtaining a desired crystal size without a wide crystal size distribution, the crystallization should be effected in such a manner that the supersaturation of the mother liquor remains below 1.3 (preferably 1.2) with respect to lactitol throughout the crystallization.
  • the supersaturation can be maintained within a desired range either by using a sufficiently long crystallization time or by measuring the dry substance content of the mother liquor with a refractometer.
  • the supersaturation can be calculated from the dry substance content of the mother liquor and from the solubility curve of lactitol.
  • Monohydrate anhydride Lacty-M, LCDE-31 partially restored during storage and having a melting range 97-103°C corresponding to 2% anhydration was cloddy and possessed a hygroscopity substantially greater than that of the monohydrate (from Test 2 in Example 1). Water absorptions at 20°C after storage for 3 days at various relative humidities are shown in the following Table I.
  • Drying tests were carried out on lactitol monohydrate in a conventional laboratory oven at a pressure of 1 bar. The samples were weighed and the degree of anhydration was calculated as a function of the drying time. Table II shows the degree of anhydration under varying drying conditions.
  • the melting ranges of the partially anhydrated monohydrates formed in the test are 100-146°C (cf. Example 3).
  • the new lactitol monohydrate is particularly suitable as a substitute for sugar in diabetic, dietetic or tooth-friendly products.
  • lactitol monohydrate with other bulk or intense sweeteners, such as saccharin, Aspartame, Acesulfame K, Alitane, Sucralose, Stevioside or xylitol, a product highly resembling sugar and yet having a lower energy content and further being tooth-friendly can be prepared.
  • this product is novel, and can be used instead of sugar e.g. in sugar products, confectionery, jams, bakery products, table-top sweeteners, cereals, desserts, chocolate, beverages, chewing gum and ice-creams, as well as in pharmaceutical and cosmetic products, such as toothpaste.
  • a four-step crystallization test sequence was carried out on lactitol monohydrate, starting from a filtered and de-ionised lactitol solution.
  • the lactitol solution had been prepared from a lactose solution hydrogenated by the conventional technique.
  • the crystallization was carried out according to the following steps: A lactitol solution having a purity of 98.3% lactitol in the dry matter was evaporated to 82.1% by weight at a temperature above 70°C, and 423 kg thereof was transferred into a crystallizer.
  • the crystallizer was a conventional horizontal cylindrical batch-operated cooling crystallizer having a volume of 0.4 m3 and provided with a mixer and a recycling water jacket whose temperature was controlled by means of a microprocessor.
  • the temperature of the solution was adjusted to 70°C, whereafter the solution was seeded with ground lactitol monohydrate crystals.
  • the seed crystal size was 0.02-0.05 mm, and the quantity thereof was 0.004% by weight on the lactitol in the batch. After the seeding, the mass was cooled in 16 hours down to 40°C, first slowly and ultimately more rapidly.
  • the crystals were separated from the mother liquor with a conventional basket centrifuge wherein the crystals were also washed using 9.2% of water per obtained amount of crystal product.
  • the centrifuged crystals were dried with a drum dryer using the conventional technique.
  • the diameter of the cocurrent drum dryer used was 0.6 m, height 2.5 m and inclination about 1°; the speed of rotation was 3.5 rpm and the temperature of the drying air was 95°C.
  • the feed rate of lactitol monohydrate was about 1.2 kg/min and the delay time about 30 minutes.
  • the total yield of lactitol monohydrate (four-step crystallization) was 97.6 %.
  • Crystallization Example 1 is intended to illustrate the practicability of the novel process, but the crystallization may also be carried out by modifying it in a manner as required by normal effective production operation. Thus the crystallization may also be performed without adding seed crystals, i.e. by allowing the solution to form seeds spontaneously as in crystallization test 5. Further, the crystallization may be effected entirely or partially by evaporative crystallization as demonstrated in Example 2. The crystallization may also be carried out in a continuous operation as long as the temperature is maintained in the range 80°C-30°C and the supersaturation of the mother liquor is maintained below 1.3.
  • the lactitol solution was concentrated in a conventional 0.4 m3 evaporation crystallizer at 60°C at a pressure of about 180 mbar until the dry matter content of the solution was 80.9% by weight and there was approximately 30% of solution on the volume of the crystallizer, at which point the solution was seeded with lactitol monohydrate seed crystals.
  • the amount of seed crystals was 0.008% by weight of the lactitol monohydrate content of the final batch, and the average size of the seed crystals was about 0.03 mm.
  • more feed solution was supplied to the crystallizer, and the evaporation was continued at 59-65°C so that the dry matter content of the mother liquor was in the range 78-82% by weight.
  • the crystallizer was replete with a mass which was transferred into a cooling crystallizer and cooled from 62°C to 55°C in 10 hours, whereafter the crystals were separated from the mother liquor by centrifuging and dried as in Example 1.
  • the crystal yield was 49.7% on lactitol.
  • the purity of the lactitol monohydrate product was 99.7% on a dry matter basis, the dry matter content was 95.0% and the melting range 94.5-98°C.
  • the lactitol monohydrate produced in Test 2 of Example 1 was dried at 20-105°C with drying air having a relative humidity of 0-25% for varying periods of time, whereby different partially anhydrated monohydrates were obtained.
  • the melting range of the anhydrated monohydrates obtained is shown as a function of the degree of anhydration in Table V:
  • Example 1 Examples 2 and 3 are intended to illustrate the invention, but the crystallization can be carried out also by modifying it in a manner as required by normal effective production operation, as explained hereinabove.
  • Baked cake had golden colour and even crumb texture: Weight 275 g Height 3.7 cm Volume 744 cm Density 0.37 g/ml
  • Lactitol monohydrate 100 Fructose 40 Butterfat 40 Skimmed milk powder 110 Water 700 Emulsifier (stabiliser) (Grindstaad SE 33) 9.3 Aspartame 0.24 Colour (Bush Boake Allan Permucol egg yellow powder) 0.06 Vanilla flavour 0.4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nutrition Science (AREA)
  • Biotechnology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biochemistry (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Seasonings (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Reinforced Plastic Materials (AREA)
  • Confectionery (AREA)
EP89908709A 1988-12-01 1989-08-04 A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent Expired - Lifetime EP0456636B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE8916202U DE8916202U1 (de) 1988-12-01 1989-08-04 Kristallines Lactitolmonohydrat und Süßstoff

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FI885588A FI83965C (fi) 1988-12-01 1988-12-01 Kristallint laktitolmonohydrat och foerfarande foer dess framstaellning samt dess anvaendning.
FI885588 1988-12-01
PCT/FI1989/000142 WO1990006317A1 (en) 1988-12-01 1989-08-04 A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent

Publications (2)

Publication Number Publication Date
EP0456636A1 EP0456636A1 (en) 1991-11-21
EP0456636B1 true EP0456636B1 (en) 1996-03-13

Family

ID=8527497

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89908709A Expired - Lifetime EP0456636B1 (en) 1988-12-01 1989-08-04 A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent

Country Status (11)

Country Link
EP (1) EP0456636B1 (da)
JP (1) JP2733701B2 (da)
KR (1) KR0141981B1 (da)
AT (1) ATE135360T1 (da)
CA (1) CA1339214C (da)
DE (1) DE68925979T2 (da)
DK (1) DK170378B1 (da)
ES (1) ES2018727A6 (da)
FI (1) FI83965C (da)
NO (1) NO174555C (da)
WO (1) WO1990006317A1 (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6872414B1 (en) 1999-09-20 2005-03-29 Xyrofin Oy Anhydrous lactitol crystals, a product containing the same and a process for the preparation thereof as well as use thereof

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI91261C (fi) * 1991-03-22 1996-01-31 Xyrofin Oy Kiteinen, kidevedetön laktitoli ja menetelmä sen valmistamiseksi sekä sen käyttö
JP3035837B2 (ja) * 1991-06-06 2000-04-24 株式会社林原生物化学研究所 粉末糖質とその製造方法並びに用途
US5399365A (en) * 1991-06-19 1995-03-21 Wm. Wrigley Jr. Company Chewing gum containing palatinose and/or palatinose oligosaccharide
US5296244A (en) * 1991-06-19 1994-03-22 Wm. Wrigley Jr. Company Chewing gum containing aspartame and palatinose oligosaccharide
US5298263A (en) * 1991-06-19 1994-03-29 Wm. Wrigley Jr. Company Chewing gum coated with palatinose or palatinose oligosaccharide
US5665406A (en) * 1992-03-23 1997-09-09 Wm. Wrigley Jr. Company Polyol coated chewing gum having improved shelf life and method of making
US5270061A (en) * 1992-03-26 1993-12-14 Wm. Wrigley Jr. Company Dual composition hard coated gum with improved shelf life
FI100005B (fi) * 1993-04-23 1997-08-15 Xyrofin Oy Menetelmä välituotteen valmistamiseksi
DE4411582C2 (de) * 1994-03-30 1996-11-14 Worlee Sweet E H Worlee & Co G Kristallsüße
US5962063A (en) * 1995-11-09 1999-10-05 Xyrofin Oy Process for preparation of a crumb
CN1060320C (zh) * 1996-04-08 2001-01-10 上海淮海制药厂 一种乳糖醇溶液及制备方法
FR2753972B1 (fr) * 1996-09-27 1998-12-04 Roquette Freres Composition de lactitol et son procede de preparation
FI103120B (fi) * 1997-03-03 1999-04-30 Xyrofin Oy Menetelmä laktitolin kiteyttämiseksi
US6090429A (en) * 1997-03-27 2000-07-18 Roquette Freres Process for the manufacture of a lactitol syrup
FI107732B (fi) 1998-03-18 2001-09-28 Xyrofin Oy Laktitolin kiteyttäminen, kiteinen laktitolituote ja sen käyttö
WO2000024273A1 (en) * 1998-10-28 2000-05-04 San-Ei Gen F.F.I., Inc. Compositions containing sucralose and application thereof
FI20022130L (fi) * 2002-12-03 2004-06-04 Danisco Sweeteners Oy Menetelmä syötävien päällystettyjen ytimien valmistamiseksi ja menetelmällä valmistetut ytimet
WO2004087648A2 (en) * 2003-03-12 2004-10-14 Sun Pharmaceutical Industries Limited Stabilized phenytoin containing composition
KR101189640B1 (ko) 2010-03-26 2012-10-12 씨제이제일제당 (주) Ｄ-사이코스 결정을 제조하는 방법
GB2495157A (en) * 2011-09-20 2013-04-03 Nihon Kraft Foods Ltd Extruded confectionery comprising filled capillaries

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2133428C3 (de) * 1971-07-05 1975-01-16 Maizena Gmbh, 2000 Hamburg Verwendung von Lactit als Zuckeraustauschstoff
NL176042C (nl) * 1978-11-13 1985-02-18 Cca Biochem B V Werkwijze ter bereiding van luchtige banketprodukten voor diabetici.
NL8002823A (nl) * 1980-05-14 1981-12-16 Amsterdam Chem Comb Lactitolmonohydraat, alsmede werkwijze voor het bereiden van kristallijn lactitol.
JPS5885900A (ja) * 1981-11-17 1983-05-23 セ−セ−ア−・ビオヘム・ベ−・ヴェ− ラクチトール水和物結晶の製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Abstract of a paper presented by M.VAN BOMMEL and J.A.KANTERS at the 6th Europ.Cryst. Meeting, Barcelona on July 28, 1980 *
INTERNATL. DAIRY FEDERATION BULLETIN, vol. 212, 1987; C.J. BOOY, pp. 62-68 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6872414B1 (en) 1999-09-20 2005-03-29 Xyrofin Oy Anhydrous lactitol crystals, a product containing the same and a process for the preparation thereof as well as use thereof

Also Published As

Publication number Publication date
FI83965C (fi) 1991-09-25
JP2733701B2 (ja) 1998-03-30
FI83965B (fi) 1991-06-14
EP0456636A1 (en) 1991-11-21
ES2018727A6 (es) 1991-05-01
DE68925979D1 (de) 1996-04-18
NO912030D0 (no) 1991-05-27
WO1990006317A1 (en) 1990-06-14
ATE135360T1 (de) 1996-03-15
DE68925979T2 (de) 1996-08-14
FI885588L (fi) 1990-06-02
NO174555C (no) 2007-03-19
DK170378B1 (da) 1995-08-14
KR900701809A (ko) 1990-12-04
NO912030L (no) 1991-07-02
FI885588A0 (fi) 1988-12-01
KR0141981B1 (ko) 1998-06-15
DK104191D0 (da) 1991-05-31
CA1339214C (en) 1997-08-05
NO174555B (no) 1994-02-14
DK104191A (da) 1991-05-31

Similar Documents

Publication Publication Date Title
EP0456636B1 (en) A crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent
US5672589A (en) Crystalline lactitol monohydrate and a process for the preparation thereof, use thereof, and sweetening agent
US5779806A (en) Crystalline anhydrous lactitol and a process for the preparation thereof as well as use thereof
US6555146B1 (en) Sugar-free foodstuff products
JPH04503504A (ja) 結晶性ラクチトール一水和物およびそれらの製法、それらの用途、および甘味料
US6548095B1 (en) Sugar-free compressed products
CA2200713A1 (en) Food products with low calorie bulking agent
EP0981533B1 (en) A process for the crystallization of lactitol
US6872414B1 (en) Anhydrous lactitol crystals, a product containing the same and a process for the preparation thereof as well as use thereof
WO1989004609A1 (en) Bulking agent
JP2002112709A (ja) 冷菓及びその製造方法
DE8916202U1 (de) Kristallines Lactitolmonohydrat und Süßstoff
EP1214329A1 (en) Anhydrous lactitol crystals, a product containing the same and a process for the preparation thereof as well as use thereof

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19910517

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: SUOMEN XYROFIN OY

EL Fr: translation of claims filed
TCAT At: translation of patent claims filed
TCNL Nl: translation of patent claims filed
DET De: translation of patent claims
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: XYROFIN OY

17Q First examination report despatched

Effective date: 19921211

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE FR GB IT LI LU NL SE

REF Corresponds to:

Ref document number: 135360

Country of ref document: AT

Date of ref document: 19960315

Kind code of ref document: T

ET Fr: translation filed
REF Corresponds to:

Ref document number: 68925979

Country of ref document: DE

Date of ref document: 19960418

ITF It: translation for a ep patent filed
PLBQ Unpublished change to opponent data

Free format text: ORIGINAL CODE: EPIDOS OPPO

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

26 Opposition filed

Opponent name: PURAC BIOCHEM

Effective date: 19961211

NLR1 Nl: opposition has been filed with the epo

Opponent name: PURAC BIOCHEM

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLBO Opposition rejected

Free format text: ORIGINAL CODE: EPIDOS REJO

APAC Appeal dossier modified

Free format text: ORIGINAL CODE: EPIDOS NOAPO

APAE Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOS REFNO

APAC Appeal dossier modified

Free format text: ORIGINAL CODE: EPIDOS NOAPO

APAC Appeal dossier modified

Free format text: ORIGINAL CODE: EPIDOS NOAPO

REG Reference to a national code

Ref country code: GB

Ref legal event code: CTFF

Free format text: GBCTFFSPC/GB2000/023, 20000915

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

REG Reference to a national code

Ref country code: GB

Ref legal event code: CTFG

Free format text: GBCTFGSPC/GB00/023: 20020502, EXPIRES: 20131206

APAC Appeal dossier modified

Free format text: ORIGINAL CODE: EPIDOS NOAPO

PLBN Opposition rejected

Free format text: ORIGINAL CODE: 0009273

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: OPPOSITION REJECTED

27O Opposition rejected

Effective date: 20021209

NLR2 Nl: decision of opposition

Effective date: 20021209

APAH Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNO

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 20080829

Year of fee payment: 20

Ref country code: CH

Payment date: 20080825

Year of fee payment: 20

Ref country code: NL

Payment date: 20080824

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20080818

Year of fee payment: 20

Ref country code: AT

Payment date: 20080721

Year of fee payment: 20

Ref country code: IT

Payment date: 20080827

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20080827

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20080930

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20080922

Year of fee payment: 20

Ref country code: SE

Payment date: 20080827

Year of fee payment: 20

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20090803

BE20 Be: patent expired

Owner name: *XYROFIN OY

Effective date: 20090804

NLV7 Nl: ceased due to reaching the maximum lifetime of a patent

Effective date: 20090804

EUG Se: european patent has lapsed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20090803

Ref country code: NL

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20090804

REG Reference to a national code

Ref country code: GB

Ref legal event code: CTFL

Free format text: PRODUCT NAME: LACTITOL MONOHYDRATE; REGISTERED: FI 13541 19981207; UK PL 17154/0001 20000324; REASON FOR LAPSE: SURRENDERED

Spc suppl protection certif: SPC/GB00/023

Filing date: 20000915

Effective date: 20100205

REG Reference to a national code

Ref country code: GB

Ref legal event code: SPCX

Free format text: SPC/GB00/023 IS INCORRECTLY SHOWING AS SURRENDERED, BUT THEY SHOULD BE SHOWING AS FEES NOT PAID IN THE REASON FOR LAPSE SECTION.

Spc suppl protection certif: SPC/GB00/023